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As with so many things in Pepper's life, it begins with Tony complaining. Snarking and sighing as he rolls out of bed in the wee hours of the morning to pick up a call from Peter Parker's aunt, then huffing and growling through a call from Happy an hour later as he stumbles back to catch an extra twenty minutes before their mutual alarms go off.

Pepper rolls to tuck against Tony's side. "What'd the kid do?"

There's an exasperated growl as Tony's face presses comfortably against her neck. "Got himself stuck in a storm drain. A storm drain!"

Pepper buries a drowsy chuckle in her pillow. It isn't unusual at this point. The kid is nothing if not talented at finding new and endearing ways to get himself into trouble. It’s sweet. And she can’t help being grateful when the emergencies on the other end of Tony’s phone calls are goofy teenage shenanigans instead of world crises.

"He okay?"

"Peachy," Tony mutters around a yawn. "Got his aunt all fired up when he missed curfew and got Happy all fired up when his little patrol report thing cut out mid-sentence."

"Poor Peter." She has yet to meet May Parker, but if the woman can keep Tony properly intimidated, there was no doubt that tonight wouldn't be a fun night to be Peter. Even less so, if Happy manages to get his hands on him. A worried Happy was never a pleasant Happy, and she can only imagine that news of his favorite teenage headache getting stuck in the city’s sewer system would throw his worry-wart tendencies into overdrive.

"No, no, no. He gets no sympathy for this. If anybody does, I do for having to handle the mother hens. I swear, someday I'm gonna set those two up—they can fuss at each other instead of me."

Pepper laughs outright. As if Tony isn’t the worst of the bunch himself. His brow softens in a tacit admission that he knows it, too, but will never ever deign to say it out loud. She presses a kiss to the tip of his nose.

"Don't meddle."

"Hey, it's good plan! Hap’s got a crush on her already…He needs to get out more, May needs more reasons not to yell at me—it'll be great."

Pepper hums an unconvinced retort. As much as she values good strategy or a bit of healthy planning ahead, matchmaking doesn’t often appeal to her. It feels intrusive and risky in a way that pulling the strings of an important merger or plotting out the moves of a chess game six moves ahead doesn't, with far fewer rewards attached to the game. She's never seen a set-up that lasted very far beyond the first few stilted dinners and casual nights, but has seen plenty that end in bruised feelings and awkward situations.

But, she supposes, the odds that Tony will ever follow-through with that idea is slim to nil. He has a million flashes of prospective genius every day; no one has time to test them all.

"Tony," Pepper tugs the duvet further up her shoulders and lets her eyes fall shut, still smiling faintly. "Go back to sleep."

*

Years pass before she contemplates May Parker and Happy Hogan again. Long years and breathless battles and both the greatest tragedy and the greatest triumph of the universe. And Tony right along with them.

 The funeral passes in a blur, too, Pepper with too much on her own mind to focus too heavily on what goes on around her. The Parkers, however, are an exception, mostly because Pepper feels responsible for the devastated teenager she tugs home to the lakehouse after the dust of the battlefield settles. She's there when May arrives a day afterwards, beelining from the car Happy hired to catch Peter in a desperate embrace that makes his face crumple into tears all over again. Pepper moves to turn away to give their reunion a little privacy, but doesn't manage it before May catches her eye with a look of understanding so clear that Pepper's breath catches. It strikes her that May is also a widow, and she suspects that—even though they have yet to make any proper introductions—May will be a much easier guest than the rest of the horde of gods and aliens and heroes that have crowded under her roof. May, at least, knows the territory.

The Parkers stay for a week following the memorial, in no small part due to Morgan—who, upon spotting the only person who isn't six feet tall and mildly terrifying among the people who have invaded her home—latching onto Peter like a limpet as soon as the two become acquainted. May puts up a token protest at first, but with both the knowledge that their apartment in Queens is long gone and that all of them are floundering in the wake of...everything...she soon drops it.

Pepper isn't sure they would've survived that week without her.

 The household tasks pushed to the back burner by the turmoil are done before Pepper has time to think about them. The kids, both of them still in a numb sort of shock, are shepherded to bed at the appropriate times and plied with sandwiches and mac and cheese and the other simple staples from May's repertoire, even though neither of them does much more than pick at whatever's put in front of them. The rest of them aren't much better, but Pepper keeps finding mugs of tea pressed into her hands and plates of food within easy reach as she tries to sift through the mountain of tasks that pile up in her inbox while she’s trying to remember to keep breathing through the calm façade she’s been clinging to like a lifeline.

Happy, who hasn't strayed further than the one-stoplight town five miles up the road for cheeseburger runs since the funeral, gets the same treatment while he does his best to maintain some semblance of order amid the chaos. He’s the one helping field the phone calls and keep the world with its clamoring journalists and stockholders and department heads at bay. It's with no small relief that Pepper catches glimpses of May passing him a coffee as he slips out onto the porch with a phone to his ear, of him being coaxed into the kitchen to sit long enough for a cup of soup, of him discreetly snorting into a Kleenex from one of the little disposable packages May leaves out as if she has some uncanny sense for how often one or the other of them will crack a little under the pressure.

By the time the week is up and a new apartment for the Parkers has been scouted out and vetted and the first few months' rent paid for before May can put up a fight, everyone is attached and Morgan is flinging her arms around Peter's neck as if she's the sticky one whenever the topic of leaving comes up. When the day comes, May—who has also been quickly adopted as a newfound favorite aunt—helps Pepper pry her gently off with promises of all the video chats Morgan wants and weekend visits whenever they can manage it. Pepper thanks her as Peter takes Morgan’s hand to walk her back inside, and May shrugs, that soft look of understanding that wasn't quite a smile flickering over her face.

"It isn't my first go-round with funerals that shouldn't have happened and kids who haven't quite grasped the reality yet. Peter was just as clingy after his...well. After."

Pepper nodded. She could understand that. She hadn't quite grasped the reality, either.

The gravel crunched underfoot a few yards away, and Pepper looked up to see Peter back and hovering there with his hands in his pockets and that same stoically blank look carved into his face as he murmured that the car was ready. A part of her broke at that—it was the same fragile sort of look Morgan wore when she was trying to outstubborn a bout of tears. She had the feeling he would shatter later, when he and May were away from the extra people and there had been time to process the whirlwind they were all trying to survive. But for now, he was in the same boat Pepper was: muddling through until there was actually some time to grieve. She curls her arms around him tight when they say their goodbyes, hoping that he weathers the storm better than she currently is.

"Here," May pressed a card into Pepper’s hands when she clasped them in a harried goodbye. Pepper turned it over to scan the number and email address. "In case you want an ear sometime. Or a shoulder."

Pepper murmured her thanks before Happy appeared to escort them to the waiting car, watching from the porch as he clasps the kid to his side in the stiff bodyguard equivalent to a hug and offers a hand to May. She takes it in both of hers and squeezes, that same understanding in her eyes when Happy squeezes back. The clasp of hands stretches out a few seconds longer than Pepper's had. It isn't enough to seem strange, but it’s enough to pull at some long-forgotten thread of memory. To dredge up a joke long since forgotten and the image of Tony's scheming smirk flashing in hazy pre-dawn light. Pepper flinches at the dagger-sharp pang in her chest; it comes with every memory, every reminder of what's gone. It's going to kill her before the day's out if it goes on at this rate, given that—after so many years—there is no part of her life that doesn't have a piece of Tony tied to it.

 She sees Happy swallow hard as he glances down at the kid, who hasn't even tried to squirm out of his grip yet, and reluctantly releases him. Pepper had seen that reluctance a lot lately. He hovers close to all of them, trying his best to keep an eye on her, on Morgan, on Rhodey, on Peter, all at once. It's an impossible task, but Pepper doesn't blame him. The last time he'd let Tony out of his sight had led to this. A memorial floating out on the lake and an empty spot in their midst. She isn't keen to let anyone else out of her grip, either.

At least now it looks like she won't have to. She'd worried, at first, about what all of this would mean when it came to the kid. He was as much a part of the family as Happy and Rhodey were. As much Tony's child as Morgan was. But without Tony there, she had feared the family might...drift. Particularly if his aunt was spooked by this brutal reminder of how things could end for men in masks. She turns May Parker's card over in her palm and scans the number for future reference. After finally meeting the woman in question, she supposes she needn't have worried. May seems the sort to take it all in stride when faced with the sort of life her child had chosen to live. Pepper could appreciate that. And could see places where that would fit right into their little circle.

*

Shifting all Parker-related tasks onto Happy's calendar is a strategic move in more ways than one. Someone would have to handle processing the items designated for Peter in the will, someone would have to look into delivering the containment unit for the Iron Spider suit, and—most importantly—someone would have to keep tabs on Spider-Man's activities going forward: it might as well be Happy. Mostly because he has the most experience in looking after Peter, but...perhaps a little because Pepper is curious.

It's an experiment. A gentle little test to see what would happen to those two with a little extra time, a little shared experience...It wouldn't do anyone any harm, and if Pepper is right—and she usually is—it might do a good deal of good in the long run.

It isn’t meddling.

Not really, she decides, even as she hears the echo of Tony snickering in the back of her mind and breathes deep through the familiar gnawing ache in her chest that comes with it. She isn’t “setting them up” the way he mused about, she’s just…delegating tasks the same way she always does. And if it leads to any unexpected results, well…that’s up to them.

But she's getting ahead of herself.

She marks down a tentative moving date for Happy to deliver the containment unit in the shared calendar and jots a note suggesting that he arrange to drive it over during business hours if May is amenable. Fewer prying eyes around the apartment building. And, more importantly for her purposes, Peter would be at school. Not that she thinks he would mind those two spending a little time together in the long run, but...it doesn't seem like something for him to concern himself with just yet. Not with so much of his world crumbled around his ears. Pepper makes a mental note to text him later and extend the offer to come spend some time with Morgan now that they're settled into the New York penthouse again. The world wouldn't be the same no matter what they did. But there was no rebuilding that crumbled mess if they didn't start somewhere.

*

Delivery day comes and Happy spends nearly four hours in Queens, which is longer than Pepper would've expected for a simple drop-off and set-up. Raised brows prompt a blustery explanation involving a broken elevator, a herculean team struggle up three flights of stairs, and thank-you cookies that, by Pepper’s calculations, must have taken a solid two hours to eat. Pepper smiles at the tinge of red around Happy’s ears as he beats a hasty retreat from that conversation and marks the day down as a success.

*

May worries in the months that follow. Pepper reads it in the lines of her face and the tension of her smile when they meet for wine and some adult conversation that doesn't revolve around either of their respective jobs. With Peter out on the streets so soon and without the once ever-present promise of back-up from Tony if he ever needed it, Pepper can't blame her. There's little Pepper can offer apart from support from Rescue if something dire arises (something about that thought turns her insides even as she offers—she would wear the suit again in a heartbeat if one of the family was on the line, but she would never feel as at home wrapped in metal and circuits as he did) and Happy's full attention whenever May has questions. At the moment, there's no one who knows Spider-Man's comings and goings better. Pepper knows for a fact that Peter still calls him to deliver "reports" about his nightly outings, although she suspects the phenomenon of Happy actually picking up the phone rather than letting it ring through to voicemail is a new development. So far as she can tell from the sporadic text conversations she makes sure to maintain with the kid, Happy is also the one who fields any calls for rides when the web fluid runs out or for bandages when his luck doesn't quite hold out. If anyone can keep May in the loop, it's him.

But May waves off Pepper's attempt to give her Happy's private number with a smile and the reassurance that she already has it. Pepper bites back a stab of pleased curiosity as she wonders how that came about. Keeping Peter safe was the focus of the conversation, of course, but this was...interesting. May's thoughtful look at Pepper’s suggestion might indicate that she hadn't used the number much just yet, but the fact that she had it at all spoke volumes. Happy kept that number quieter than most of the company secrets. Pepper smiles as she hugs May good night and sees her out to the private elevator.

Over the course of the next few months, she sees Happy striding through his duties with his phone nestled against his shoulder much more often. Some of it is to be expected in the wake of the upheaval that strikes Stark Industries with the loss of Tony, but when Happy’s business-like scowl is conspicuously absent, it’s easy to guess who’s on the other end of the line.

Perhaps, Pepper muses, this is less meddling and more...observing. It seems that whatever is happening would likely have happened just the same without her interference.

Still, that doesn’t mean she has to stop.

*

The...observing...becomes easier when May launches her charity work. Pepper throws in her full support, of course, and makes a few appearances at various events as her schedule allows, but Happy is the one she appoints as the official Stark Industries liaison. He doesn't protest when Pepper hands off the baton, the stoic veneer cracking a little when she asks if he minds piling another responsibility on his plate and he shakes his head a little too fast, stumbling over his assurances like a schoolboy.

The events themselves are often better attended than the galas and benefits Pepper remembers from before the so-called Blip. Unlike the litany of other causes she's supported over the years, there's no one in the world—in the universe—that this one doesn't touch in one way or another. The venues aren't as lavish and the banquets aren't as decadent—May isn't a wasteful person—but the tickets always sell and the donation totals are always good. Pepper makes sure of it. And when she can't manage it in person, Happy is always there to take her place delivering checks and attending the dinners and helping May plan out the next ones. May doesn't protest when Pepper apologizes for not having the spare time to meet to discuss sponsorship plans face-to-face, and Happy doesn't protest when Pepper offers up her standing reservations from that cozy little Italian place in Brooklyn for the two of them to strategize over dinner.

She only has to do it once. After that, she knows the dinners happen, but they make their own reservations. All for charity business, Happy declares, whilst setting up a table for two on a Friday night. Pepper nods solemnly and thanks him for his dedication, tamping down a faint smile as she does it.

*

Rhodey zeroes in on it from a mile away, sauntering up to Pepper's side at one of the bigger events to nod their direction and waggle his eyebrows. Pepper merely smiles and sips her champagne. Rhodey chuckles, a pensive smile unfurling on his face, too, as he looks on.

"You know he'd be having a field day with that."

"I know," Pepper murmurs over the sting behind her ribcage. It waxes and wanes, a knife in her ribs sometimes and a dull, throbbing reminder at others. But it’s easier in places like this, with most of the people she has left clustered in one happy place.

"It's cute," Rhodey continues, watching Happy beam at May's smile when he dutifully extends an arm for her to lean on and a hand to hold her glass while she balances on one foot to adjust a misbehaving heel. Per the snippets of gossip Pepper had picked up mingling on gala event floors and backstage before her own guest appearances, half the other volunteers already believed they were more than coworkers based on the sheer frequency of Happy’s presence at leaflet drops and phone drives and anywhere else May happened to be. Not to mention how often May would absently reach over to straighten his tie or order take-out for two to prolong those visits at her office at the charity’s home base. And really, given the way those two had taken to making eyes at each other over their stacks of brochures and piles of sponsorship packets when each thought the other wasn’t looking, Pepper couldn’t blame the gossip mill for firing up. They weren’t subtle.

"It is cute." Pepper slides a glance over at Rhodey to find his eyes narrowing with the shrewd humor she'd grown to appreciate over the years. "So be nice."

He grins, just enough mischief in his smile to make it entirely certain that he's going to corner Happy for a bit of good-natured heckling later, and raises his glass in salute.

"You have your fun, and I have mine."

*

Pepper had to check the message twice to be sure she had read it correctly. An afternoon off wasn't too unusual for most, but for Happy Hogan, it was unprecedented. In the past twenty odd years, she'd yet to see him take much voluntary (the hospital stays during the Mandarin incident and that brush with appendicitis aside) time off apart from his Downton Abbey nights. His focus was part of his charm and for Happy, there was little better to focus on than his job. And yet here he was in her inbox, checking in to see if Pepper needed anything before he slid out a few hours early. There was a conspicuous lack of explanation, apart from a separate text from Peter asking if he could take her up on the Morgan-sitting offer tonight since he was free (and in need of distraction, if Pepper read the subtext correctly). May, evidently, was going to be out for the evening. Pepper smiled and tapped out replies to Happy and Peter respectively.

Have fun.

*

It became a routine by the end of the month. Not always the same time or the same day each week, but often enough for Pepper to expect Happy's guilty-eyed questions about whether she or Morgan needed him for the evening and his shifty responses when asked if he had big plans. Pepper does her best to make sure she can oblige, keeping most nights as clear as she can on the Asset Management front and relying on Peter a little more for looking after Morgan where she might otherwise have left her with Happy.

It’s well worth it in her opinion. He always comes back to work with poorly hidden stars in his eyes and less of a droop to his shoulders. A little brighter, a little less weighed down by the grief they'd all been hauling around. Pepper turns away to hide her smiles and makes sure his schedule is loose enough to clear at least one evening the following week, too. Happiness—even in small doses—is hard to come by in the aftermath. And if anyone in her little circle can find a scrap of it, Pepper has no qualms about helping it along when she can. Once upon a time, she might’ve disapproved of meddling, but she sees the merit in it more clearly now.

…Even though she still clings to her own internal argument that she’s—mostly—done little more than observe.

*

It's hard to gauge whether or not it will last. Apparently, they call it "a summer fling" when Peter finds them out, a fact he spills to Pepper with a theatrical shudder that makes her laugh harder than she has in a long time. Peter shakes his head from his perch on her countertop, where he sits drinking coffee while Morgan naps after one of their little playdates, and gives her a look of offended disgust so exaggerated he can barely hide the smile underneath it. It's enough to answer the question of whether Peter truly objects without Pepper even having to broach the subject. That comes as an enormous weight off her mind. She didn’t expect it to be a problem, really—Peter is as much a part of Happy’s family as Pepper is at this point and vice-versa, if Peter’s playful bickering with him is any indication—but it’s nice to have some certainty.

 Still, if Pepper had to wager on it, she'd say they have a fighting chance. When Beck took aim at Peter with his dying breaths, it was May and Happy that roared to his defense, storming into her office for a strategy meeting in a united front that even Pepper found a little impressive. That sort of teamwork under pressure isn't to be taken lightly. Pepper would know. And perhaps it had less to do with any romantic feelings and more to do with their common affection for the kid, but only time would tell. For now, Pepper was content to call it a job well done and be happy that there was at least a bit more fleeting contentment in the world.

She catches a glimpse of them strolling arm-in-arm around the dock during the long weekend the extended family takes to recoup after the firestorm surrounding Spider-Man's reveal settles and smiles. Whatever they were now, she can't regret pulling a few strings in the beginning. It puts a definitive checkmark by one of the many, many projects Tony left behind: get Happy Hogan a girlfriend. Several projects, really, if she counts his half-hearted joke about setting up Peter's primary caregivers to get them both off his back. Either way, it feels like the sort of scheme Tony would have approved of. Pepper's smile softens at that as she turns back to the cabin to give the couple their privacy, the twinge behind her sternum flaring as it always does with the thought of his grin. Her heart doesn’t clench as much at times like these, when it feels like he could be snickering over her shoulder at a project they could have shared.

But, she supposes, that’s one more reason she couldn't regret meddling (she’s given up on calling it anything else) a little. The distraction wasn't only good for Happy and May. And she doesn't mind the memories.